A composition for forming a resist underlayer film is provided, which contains: a calixarene-based compound obtained from a calixarene by substituting at least a part of hydrogen atoms each on phenolic hydroxyl groups comprised in the calixarene, with a monovalent organic group having 1 to 30 carbon atoms; and an organic solvent. The monovalent organic group preferably includes a crosslinkable group. A part of hydrogen atoms each on phenolic hydroxyl groups of the calixarene-based compound is preferably substituted. The ratio of the number of substituted phenolic hydroxyl groups to the number of unsubstituted phenolic hydroxyl groups in the calixarene-based compound is preferably no less than 30/70 and no greater than 99/1.
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1. A composition comprising: a calixarene-based compound represented by formula (3); and an organic solvent, wherein in the formula (3), R represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms, and at least one R is the monovalent organic group; m is an integer of 4 to 12; Y represents a hydrocarbon group having 1 to 10 carbon atoms; q is an integer of 0 to 7; p is an integer of 1 to 3, wherein a sum of p and q is no less than 1 and no greater than 8; and k is 0 or 1; X represents a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom, wherein a plurality of Rs are identical or different, a plurality of Xs are identical or different, a plurality of “k”s are identical or different, a plurality of “p”s are identical or different, and a plurality of “q”s are identical or different, and wherein in a case where Y is present in a plurality of number, a plurality of Ys are identical or different, wherein, in a case where p is 2, X is a phenyl group substituted with —OR; or the monovalent organic group represented by R is at least one group selected from the group consisting of a benzyl group, a cyclopentyl group, a group comprising a polymerizable carbon-carbon triple bond, a group comprising an epoxy group, a group comprising an alkoxymethyl group, a group comprising a formyl group, a group comprising an acetyl group, a group comprising a dialkylaminomethyl group, a group comprising a dimethylolaminomethyl group, a group represented by formula (a), a group represented by formula (b), and group represented by formula (c): wherein R a and R a′ each independently represent a single bond or an alkanediyl group having 1 to 10 carbon atoms; R a″ represents a single bond, an alkanediyl group, a hydroxyalkanediyloxy group or (R″O) i ; R″ represents an alkanediyl group; “i” is an integer of 1 to 10; R b″ represents a hydrogen atom; and R b , R b′ , R c , R c′ , R c″ , R d , R d′ and R d″ each independently represent a hydrogen atom or a monovalent hydrocarbon group, wherein at least one monovalent organic group represented by R is the group represented by the formula (b).
A composition for creating a resist underlayer film used in semiconductor manufacturing comprises a calixarene-based compound and an organic solvent. The calixarene compound is defined by a specific chemical formula (3) with multiple variable substituents (R, Y, X) and integer parameters (m, q, p, k). At least one R group is a monovalent organic group (1-30 carbons). This R group can be a benzyl, cyclopentyl, polymerizable carbon-carbon triple bond, epoxy, alkoxymethyl, formyl, acetyl, dialkylaminomethyl, dimethylolaminomethyl group, or a group represented by formula (a), (b), or (c). Crucially, at least one R group *must* be represented by the formula (b).
2. The composition according to claim 1 , wherein a part of hydrogen atoms on phenolic hydroxyl groups of the calixarene-based compound is substituted.
The composition for a resist underlayer film, which comprises a calixarene-based compound and an organic solvent (as described in claim 1), has the additional feature that *some*, but not all, of the hydrogen atoms on the phenolic hydroxyl groups of the calixarene-based compound are substituted with other chemical groups. This means some of the -OH groups on the calixarene molecule have had the H replaced.
3. The composition according to claim 2 , wherein a ratio of the number of substituted phenolic hydroxyl groups to the number of unsubstituted phenolic hydroxyl groups in the calixarene-based compound is no less than 30/70 and no greater than 99/1.
The composition for a resist underlayer film, containing a calixarene-based compound and an organic solvent, where *some* hydrogen atoms on phenolic hydroxyl groups of the calixarene are substituted (as described in claims 1 and 2), has a specific substitution ratio. The ratio of substituted phenolic hydroxyl groups to unsubstituted phenolic hydroxyl groups within the calixarene-based compound must fall between 30/70 and 99/1.
4. The composition according to claim 1 , wherein the calixarene-based compound is derived from a compound obtained by subjecting a compound represented by formula (1) and a compound represented by formula (2) to a condensation reaction, wherein in the formula (1), Y, k, p and q are as defined in the formula (3), and wherein in the formula (2), X is as defined in the formula (3); and j is 1 or 2.
This invention relates to a chemical composition featuring a calixarene-based compound designed for molecular recognition or binding applications. The problem addressed is the need for highly selective and efficient binding agents, particularly in fields like environmental remediation, drug delivery, or analytical chemistry, where precise molecular interactions are critical. The composition includes a calixarene-based compound derived from a condensation reaction between two specific compounds: one represented by formula (1) and another by formula (2). In formula (1), the structure includes variable groups Y, k, p, and q, which are defined by a broader formula (3). Similarly, formula (2) contains a variable group X, also defined by formula (3), and a variable j, which can be either 1 or 2. The condensation reaction between these compounds produces a calixarene derivative with tailored binding properties. The calixarene-based compound is engineered to enhance selectivity and affinity for target molecules, leveraging the unique three-dimensional cavity structure of calixarenes. This allows for applications in molecular encapsulation, sensing, or separation processes. The invention focuses on optimizing the synthesis pathway to improve yield, purity, or functional performance of the resulting calixarene derivative. The composition may be used in solutions, coatings, or composite materials depending on the application.
5. The composition according to claim 1 , wherein a molecular weight of the calixarene-based compound is no less than 500 and no greater than 3,000.
The composition for a resist underlayer film, which comprises a calixarene-based compound and an organic solvent (as described in claim 1), has a calixarene-based compound with a molecular weight between 500 and 3,000. This range defines the size of the calixarene molecule used in the composition.
6. The composition according to claim 1 , wherein the organic solvent comprises a polyhydric alcohol partial ether acetate solvent, a ketone solvent, a carboxylic acid ester solvent, or a mixed solvent thereof.
In the composition for a resist underlayer film comprising a calixarene-based compound and an organic solvent (as described in claim 1), the organic solvent can be one or more of the following: a polyhydric alcohol partial ether acetate solvent, a ketone solvent, or a carboxylic acid ester solvent. The solvent dissolves the calixarene-based compound, allowing for film formation.
7. The composition according to claim 1 , further comprising a resin other than a resin corresponding to the calixarene-based compound.
The composition for creating a resist underlayer film, which comprises a calixarene-based compound and an organic solvent (as described in claim 1), also contains another resin *besides* the calixarene-based resin. This additional resin provides further control over the film's properties.
8. The composition according to claim 7 , wherein the resin other than the resin corresponding to the calixarene-based compound comprises a crosslinkable group.
The composition for a resist underlayer film, containing a calixarene-based compound, an organic solvent, and an *additional* resin (as described in claims 1 and 7), is further defined such that the added resin contains a crosslinkable group. This enables the resin to form crosslinks, further hardening or modifying the underlayer film.
9. The composition according to claim 7 , wherein the resin other than the resin corresponding to the calixarene-based compound comprises a novolak resin, a resol resin, a styrene resin, an acenaphthylene resin, a polyarylene resin or a mixture thereof.
The composition for a resist underlayer film comprising a calixarene-based compound, an organic solvent and an *additional* resin (as described in claims 1 and 7), has an additional resin which is one of the following: a novolak resin, a resol resin, a styrene resin, an acenaphthylene resin, a polyarylene resin, or a mixture of these. These resins are commonly used in semiconductor manufacturing.
10. The composition according to claim 7 , wherein a weight average molecular weight of the resin other than the resin corresponding to the calixarene-based compound is no less than 2,000 and no greater than 8,000.
This invention relates to a resin composition incorporating a calixarene-based compound, addressing challenges in material performance such as thermal stability, solubility, or mechanical properties. The composition includes a resin component where the weight average molecular weight of resins excluding the calixarene-based compound is controlled between 2,000 and 8,000. This molecular weight range is selected to balance processability, mechanical strength, and compatibility with the calixarene-based compound. The calixarene-based compound may function as a modifier, additive, or reactive component, enhancing properties like adhesion, thermal resistance, or chemical resistance. The resin composition is suitable for applications requiring tailored performance, such as coatings, adhesives, or advanced composites. The molecular weight constraint ensures the resin maintains sufficient flow characteristics during processing while providing adequate structural integrity in the final product. The invention may also involve additional components or processing steps to achieve desired material properties, though the focus is on the molecular weight specification of the non-calixarene resin fraction. This approach allows for precise control over the material's behavior in various environments.
11. The composition according to claim 7 , wherein a content of the resin other than the resin corresponding to the calixarene-based compound with respect to 100 parts by mass of the calixarene-based compound is no less than 5 parts by mass and no greater than 1,000 parts by mass.
The composition for a resist underlayer film comprising a calixarene-based compound, an organic solvent and an *additional* resin (as described in claims 1 and 7), has a specific concentration range for the additional resin. For every 100 parts of the calixarene-based compound, the additional resin is present in an amount between 5 and 1,000 parts.
12. The composition according to claim 1 , wherein the monovalent organic group represented by R is the group represented by the formula (b).
In the composition for a resist underlayer film comprising a calixarene-based compound and an organic solvent (as described in claim 1), the "R" substituent (monovalent organic group) in the calixarene-based compound formula *specifically* refers to the group represented by formula (b) as defined in claim 1. This narrows the definition of the "R" group to a particular chemical structure.
13. The composition according to claim 1 , wherein the organic solvent comprises a polyhydric alcohol partial ether acetate solvent, a ketone solvent, a carboxylic acid ester solvent, or a mixed solvent thereof.
In the composition for a resist underlayer film comprising a calixarene-based compound and an organic solvent (as described in claim 1), the organic solvent can be one or more of the following: a polyhydric alcohol partial ether acetate solvent, a ketone solvent, or a carboxylic acid ester solvent. The solvent dissolves the calixarene-based compound, allowing for film formation. (This is a duplicate of claim 6, but included for completeness.)
14. A pattern-forming method comprising: applying the composition according to claim 1 directly or indirectly on a substrate to provide a resist underlayer film; forming a resist pattern directly or indirectly on the resist underlayer film; forming a pattern on the substrate through dry etching of the resist underlayer film, the substrate, or both the resist underlayer film and the substrate using the resist pattern as a mask; and removing the resist underlayer film remaining on the substrate using a basic solution, wherein the method further comprises subjecting the resist underlayer film to heating or an acid treatment before removing the resist underlayer film.
A method for creating a pattern on a substrate involves using a composition including a calixarene-based compound represented by formula (3) and an organic solvent where R represents a hydrogen atom or a monovalent organic group having 1 to 30 carbon atoms, and at least one R is the monovalent organic group; m is an integer of 4 to 12; Y represents a hydrocarbon group having 1 to 10 carbon atoms; q is an integer of 0 to 7; p is an integer of 1 to 3; k is 0 or 1; X represents a substituted or unsubstituted hydrocarbon group having 1 to 30 carbon atoms or a hydrogen atom. The method includes applying this composition to form a resist underlayer film, creating a resist pattern on the underlayer, etching the substrate (and/or underlayer) using the resist pattern as a mask, and then removing the remaining underlayer film using a basic solution *after* heating or treating the underlayer with acid.
15. The pattern-forming method according to claim 14 , further comprising after providing the resist underlayer film and before forming the resist pattern: providing an intermediate layer directly or indirectly on the resist underlayer film, wherein the intermediate layer is further dry etched in forming the pattern.
A pattern-forming method, using a calixarene-based resist underlayer film (composition described in claim 14), includes applying the underlayer, *then* applying an intermediate layer on top of the underlayer, *before* creating the resist pattern. This intermediate layer is also etched during the pattern formation process.
16. The pattern-forming method according to claim 14 , wherein a part of hydrogen atoms on phenolic hydroxyl groups of the calixarene-based compound is substituted.
The pattern-forming method using a calixarene-based resist underlayer (described in claim 14), where a composition including a calixarene-based compound represented by formula (3) and an organic solvent is used, has the additional feature that *some* of the hydrogen atoms on the phenolic hydroxyl groups of the calixarene-based compound are substituted with other chemical groups. This means some of the -OH groups on the calixarene molecule have had the H replaced.
17. The pattern-forming method according to claim 16 , wherein a ratio of the number of substituted phenolic hydroxyl groups to the number of unsubstituted phenolic hydroxyl groups in the calixarene-based compound is no less than 30/70 and no greater than 99/1.
The pattern-forming method utilizing a calixarene-based resist underlayer film (as described in claims 14 and 16), where the resist underlayer film has *some* hydrogen atoms on the phenolic hydroxyl groups of the calixarene compound substituted, requires the ratio of substituted to unsubstituted hydroxyl groups to be between 30/70 and 99/1.
18. The pattern-forming method according to claim 14 , wherein the calixarene-based compound is derived from a compound obtained by subjecting a compound represented by formula (1) and a compound represented by formula (2) to a condensation reaction, wherein in the formula (1), Y, k, p and q are as defined in the formula (3), and wherein in the formula (2), X is as defined in the formula (3); and j is 1 or 2.
The pattern-forming method employing a calixarene-based resist underlayer (described in claim 14), where a composition including a calixarene-based compound represented by formula (3) and an organic solvent is used, uses a calixarene-based compound that is synthesized from a condensation reaction. This reaction involves two compounds represented by chemical formulas (1) and (2). The substituents (Y, k, p, q, X) and integer parameter (j) within these formulas are defined consistently with formula (3) of claim 14, specifying the allowable chemical structures of the starting materials.
19. The pattern-forming method according to claim 14 , wherein a molecular weight of the calixarene-based compound is no less than 500 and no greater than 3,000.
The pattern-forming method utilizes a calixarene-based resist underlayer (described in claim 14), where a composition including a calixarene-based compound represented by formula (3) and an organic solvent is used, where the calixarene-based compound has a molecular weight between 500 and 3,000. This defines the size of the calixarene molecule used in the underlayer film.
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May 19, 2016
July 4, 2017
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